Microbial Transformations of the Fungicide Cyprodinil (CGA-219417)

Schocken, Mark J.; Mao, John; Schabacker, Daniel J.

doi:10.1021/jf970298l

Cited by 27 publications

(10 citation statements)

References 19 publications

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“…For nine of the tested microorganisms a hydroxyl derivative of the substrate was obtained as a product. Beauveria bassiana ATCC 7159 was the only biocatalyst that afforded a product with O -methyl glucose attached (yield 80%), and no intermediate hydroxyl derivative was observed [ 31 ].…”

Section: Resultsmentioning

confidence: 99%

Glycosylation of 6-methylflavone by the strain Isaria fumosorosea KCH J2

et al. 2017

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Entomopathogenic fungi are known for their ability to carry out glycosylation of flavonoids, which usually results in the improvement of their stability and bioavailability. In this study we used a newly isolated strain of the entomopathogenic filamentous fungus Isaria fumosorosea KCH J2 as a biocatalyst. Our aim was to evaluate its ability to carry out the biotransformation of flavonoids and to obtain new flavonoid derivatives. The fungus was isolated from a spider’s carcass and molecularly identified using analysis of the ITS1-ITS2 rDNA sequence. As a result of biotransformation of 6-methylflavone two new products were obtained: 6-methylflavone 8-O-β-D-(4”-O-methyl)-glucopyranoside and 6-methylflavone 4’-O-β-D-(4”-O-methyl)-glucopyranoside. Chemical structures of the products were determined based on spectroscopic methods (1H NMR, 13C NMR, COSY, HMBC, HSQC). Our research allowed us to discover a new species of filamentous fungus capable of carrying out glycosylation reactions and proved that I. fumosorosea KCH J2 is an effective biocatalyst for glycosylation of flavonoid compounds. For the first time we describe biotransformations of 6-methylflavone and the attachment of the sugar unit to the flavonoid substrate having no hydroxyl group. The possibility of using flavonoid aglycones is often limited by their low bioavailability due to poor solubility in water. The incorporation of a sugar unit improves the physical properties of tested compounds and thus increases the chance of using them as pharmaceuticals.

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Section: Resultsmentioning

confidence: 99%

Glycosylation of 6-methylflavone by the strain Isaria fumosorosea KCH J2

et al. 2017

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“…Some of these metabolites had been previously found in planta in soybean, but many were difficult to synthesize and identify. In some instances, microbial cultures metabolize xenobiotics in a similar manner as plants and animals (Feng and Wratten 1989;Liu et al 1996;Schocken et al 1997). Thus, microbial in vitro systems may be good predictors of the metabolites that will be found in plants, animals, and the environment.…”

Section: In Vitro Methods For Studying Pesticide Metabolism In Plantsmentioning

confidence: 99%

Pesticide metabolism in plants and microorganisms

et al. 2003

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Understanding pesticide metabolism in plants and microorganisms is necessary for pesticide development, for safe and efficient use, as well as for developing pesticide bioremediation strategies for contaminated soil and water. Pesticide biotransformation may occur via multistep processes known as metabolism or cometabolism. Cometabolism is the biotransformation of an organic compound that is not used as an energy source or as a constitutive element of the organism. Individual reactions of degradation–detoxification pathways include oxidation, reduction, hydrolysis, and conjugation. Metabolic pathway diversity depends on the chemical structure of the xenobiotic compound, the organism, environmental conditions, metabolic factors, and the regulating expression of these biochemical pathways. Knowledge of these enzymatic processes, especially concepts related to pesticide mechanism of action, resistance, selectivity, tolerance, and environmental fate, has advanced our understanding of pesticide science, and of plant and microbial biochemistry and physiology. There are some fundamental similarities and differences between plant and microbial pesticide metabolism. In this review, directed to researchers in weed science, we present concepts that were discussed at a symposium of the American Chemical Society (ACS) in 1999 and in the subsequent book Pesticide Biotransformation in Plants and Microorganism: Similarities and Divergences, edited by J. C. Hall, R. E. Hoagland, and R. M. Zablotowicz, and published by Oxford University Press, 2001.

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“…It acts by inhibition of the methionine biosynthesis of fungi [7][8][9][10][11][12]. The fungicide exhibits an extensive metabolism in microorganisms, animals, and plants [13,14]. Besides primary metabolites and conjugates, noticeable portions of non-extractable residues are formed in plants [20].…”

Section: Introductionmentioning

confidence: 99%